In the Geography 2050 sequence, we envisioned the world of 2050, then focused on the inter-related topics of urban growth, sustainability, mobility, and next year will be energy. For each event we assemble a highly curated set of sessions and speakers that combine a geographic perspective with the academic, government, and business communities in a way that no other event replicates.

Background

In order to understand the roots of Geography 2050, and what we are trying to accomplish as the American Geographical Society (AGS), some backstory is needed. Starting four years ago, the AGS began a dramatic revitalization effort, one that would bring a significant influx of new energy, people, and ideas into the Society. Spearheaded by the now AGS Chairman, Dr. Chris Tucker, the idea of AGS 2.0 has taken root…with Geography 2050 one of its central concepts. This video, from the initial Geography 2050, describes the 2050 concept in more detail:

This synthesis is the hallmark of the AGS, and a differentiating factor in the discussions we facilitate. AGS history represents some of the best applications of the geographic perspective over the last 165 years, whether that be exploration, commerce, diplomacy, defense, or education. As we envision the role of AGS in the 21st century, we see a United States in need of greater geographic awareness. We see one role of AGS as a means to help foster a national dialogue on spatial literacy, and be a force for change in geographic education. These values are summed up well by AGS President Emeritus (and my Ph.D. advisor), Dr. Jerome Dobson, in this short video from the original Geography2050:

Highlights

The Future of Mobility event continued this trend, and the quality of sessions may have even exceeded previous years (kudos to the Dean Wise, AGS Councilor and the conference chair). It was hard not to leave the conference amazed at the pace of change in the mobility sector, and how close this next wave of technologies is to fundamentally changing how we are spatially organized. Videos for the sessions are being finalized now, and I’ll update when they are complete (see the Program here). Below are a few of my takeaways from the conference (and since I’m not an expert in mobility and transportation, I learned a tremendous amount from the sessions).

Clearly electric vehicles are already here, but when combined with longer battery life, increasing levels of automation, and “transport as a service” business models, the economics of automobile ownership and utilization change dramatically. The impact of this change on individual behavior and public planning for infrastructure leads to some widely divergent models that swing between transport utopia and massively underfunded public transportation. And this does not account for the potential of automated trucking and freight transport. We are already on the cusp of these changes, and even some of the best minds in transportation planning don’t really know what is going to happen in the next 10 years…let alone the 33 years till 2050.

Vertical take-off and landing (VTOL), flying cars, and other personal “jet pack” devices are becoming a reality. At this point, each of these are still piloted by humans, but clearly have the potential to become more and more autonomous (or remotely piloted). The already stressed regulatory environment for simply figuring out how to handle “beyond line of sight” human-flown drones, is going to be incredibly burdened as autonomous package delivery, flying taxi service, and personal VTOL devices become more common. The domestic and international airspace management regulations are incredibly complex, and accommodating these new forms of transport will be a generational challenge.

Hyperloop…wow…paradigm shift in the making. The potential of this technology is so absolutely incredible, it is truly difficult to appreciate the implications on human society. If we have any political will to accomplish great things left in this country, we should move as fast as possible towards Hyperloop. America’s bet on the automobile has been an incredible benefit to our society, and yet it has also locked us into a transport paradigm that is strangling our cities. From everything I saw, Hyperloop is the only technology that could fundamentally change the equation. The sheer speed that it travels will make disparate cities the same travel time away as current metro stops. To view some of the proposed Hyperloop routes and travel times between stops, check out the winners of the Global Route Challenge…with interactive maps.

Honoring Digital Cartography

On a personal level, this year was the first time that I’ve participated in Geography 2050 as an AGS Councilor (I spoke at the first event in 2014 before I joined the AGS Council). Having known and studied under Dr. Dobson since his arrival at the University of Kansas in 2001, I have been long steeped in AGS and its proud traditions. When Chris first proposed AGS 2.0, and started to invite new Councilors, I knew I wanted to be part of bringing new energy into the Society.

What I bring to AGS is an expertise in geographic information science and technology. Building on that background, my goal as a Councilor is to ensure AGS continues to be at the fore of geographic technology, and that the Society begin to formally recognize the contributions of those who are responsible for powering the “geospatial revolution”. Over the last 20 years geographic technologies have revolutionized our society (Global Positioning Systems, high resolution satellite imagery, in-car navigation, interactive web maps, etc…), and it is important that the Society formally acknowledge those in government, industry, and academia who contributed.

To that end, the 2017 edition of Geography 2050 marked the first attempt to do this. I believe there are many people who deserve to be honored for their contributions to the post-millennium explosion in digital geography, so nominating the right people had to be a mix of contributions and applicability to this year’s 2050 theme of mobility. Given that combination, it was clear that Brian McClendon and John Hanke were the right choices to nominate for the AGS O.M. Miller Cartographic Medal. I made the nomination, and the AGS Vice President and Chair of the Awards committee, Deborah Popper, wrote up two wonderful award letters that were read at the ceremony.

A Conversation with John Hanke and Brian McClendon

In addition to the award, both Brian and John were kind enough to participate in a Geography 2050 session, which was formatted as a conversation with them. It was an honor to moderate this session, a job that required I ask a couple opening questions and then get out of their way. I don’t get anxious speaking in front of crowds often, but have to admit, this one was a bit nerve-racking. But ultimately I think the session went well, and there was a lot of great feedback.

The goal of my questions was to first look back on their Keyhole / Google Earth experience, using it as a historical lens to view current trends. Then to discuss trends in autonomy and augmented reality that are affecting mobility. Co.Design (a Fast Company subsidiary) wrote an article on the session that has more detail.

I’d like to thank both of them personally for taking the time out of their schedules to come to New York to accept the AGS Miller Medal and participate in the panel. I certainly learned a lot, and feel that as AGS, we are off to a good start in honoring the pioneers of the modern digital geography movement.

If interested in additional information, Trajectory Magazine recently published an article on the history of Google Earth that provides great background on the evolution of the technology, and its role in the national security context.

Thanks to a generous last-minute donor, we made the $2,000 goal. Thank you to everyone who helped out, with your donations we are going to be able to diaper 2 children for an entire year. Fantastic stuff, gratitude all around.

Original Post — October 1, 2015

While a departure from the typical content on this blog, I hope you’ll spare a moment to read about a fundraising effort my wife and I put together for a cause that has grown near and dear to our hearts, the difficulty many mothers face diapering their children.

It is stunning that in this country up to 30% of mothers struggle to meet the diaper requirements of their children…30%. This stress is the leading cause of mental health problems in new mothers. And to make it worse, there is a hole in the social safety net. Traditional support programs for low-income mothers and families (WIC and SNAP) do not cover diapers and wipes. Recent stories in The Atlantic and the Baltimore Sun cover the “diaper dilemma” problem in detail. This problem has led to the creation of “diaper banks” around the country, including the DC Diaper Bank near us in Washington, DC.

Hilary and I have been humbled and amazed by having a child. So as our first daughter, Flynn, just turned a year old, we wanted to do something to help out those struggling to diaper their children. Our goal is to diaper 2 kids for a year, which costs about $2,000. This comes out to about $20 per week for 1 kid.

If anyone is interested in helping out, please visitFlynn’s 1st Birthday Diaper Drive page on GoFundMe to learn more about the issue and contribute to the cause. All funds will go to the DC Diaper Bank.

Just wanted to let everyone know that I am moving on from Boundless. It was a fascinating ride, and I learned a lot about startup life. Launching a new product is a true challenge, requiring a deft hand to manage all the constituent elements of the business. We got close, but strategic priorities required a narrower product focus. I wish everyone there well, the company has a bounty of talented people and the sky’s the limit.

Moving forward, I am going to take the next couple of months to finish my dissertation in Geography (stay tuned, lots coming on MapGive, Imagery to the Crowd, and disruptive innovation). Completing the PhD is my focus, but I’m looking forward to exploring new options. I’m open to continuing down the product management and private sector paths, but I also miss the analytical and complex emergency focus of my previous work. I’ll be reaching out to friends around town and beyond, and if anyone has any suggestions, please let me know.

With the growth in open source software, cloud computing, open data, imagery, point clouds, and the Internet of Things, there are going to be an amazing array of new opportunities for geographers. So regardless of what comes next, I will continue to use geographic data, tools, and analysis to disrupt existing workflows and business models, and strive to make the world a better place.

Back in September, the team at Government Executive did a fantasy football – inspired take on government leadership. Entitled the Dream Team, the short piece highlights eight bureaucrats found throughout the government (or formerly in the government in my case). To use the words of the GovExec authors, “here are some of the folks we’d love to see on any leadership team tackling the kinds of big problems only government can address.”

Collectively, this group has a range of skills: finance, acquisitions, program and project management, legal, IT security, HR, software platform development, disaster recovery…and somewhat curiously, two geographers.

I’m humbled to have been included on this list, particularly given the accomplishments of the other geographer, Mike Byrne. That said, what I find more intriguing is how two geographers made this list to begin with. What is it about geography that is gaining the attention of management and leadership journalists? Why would they think these are the skills needed on government teams to solve big problems? And why now?

Starting with the question of awareness, its clear that digital geography and maps have captured the public’s attention. The combination of freely available Global Positioning System (GPS), ubiquitous data networks, high resolution imagery, increasingly powerful mobile devices, and interoperable web services has fundamentally changed how the average person interacts with maps and geographic data. In the ten years since the introduction of Google Earth, the expectation of the average person is now to have complex, updated, descriptive, interactive maps at their disposal anytime, anywhere, and on any device. This shift is nothing short of revolutionary.

And while the glitz of slippy maps and spinning globes has brought the public back to maps, there is more to the story of why geographers are critical elements of multidisciplinary leadership teams. I believe there are two key characteristics that set geographers apart: Information Integration and Problem Solving. The first is the the capacity of the spatial dimension to integrate information across disciplines, and the second is how spatial logic combined with digital tools can predict, analyze, and visualize the impact of a policy decision.

Begin TL;DR

Let’s begin with the idea of information integration. At its core, Geography is a spatial science that utilizes a range of qualitative, descriptive, quantitative, technical, and analytical approaches in applications that cross the physical sciences, social sciences, and humanities. It may seem trite to say, but everything happens somewhere, so anything that involves location can be studied from a geographic perspective. Where most disciplines have fairly defined domains of knowledge, Geography, and its focus on the spatial dimension, cuts laterally across these domains.

The cross cutting nature of location is the fundamental reason why Geography is in a resurgence. Geographic location provides the mechanism to integrate disparate streams of information. Data that relates to one discipline can be linked to other data simply by its location. As a conceptual framework, Geography is an integrative lens, i.e., what are the forces that interact to define the characteristics of this location, and when combined with Geographic Information Systems (GIS) technology, spatial location acts as the relational key used to link tables of information together in a database. It is this union of mental framework and technology that provides Geography a unique capacity for information integration.

However, information is typically aggregated for a purpose, the goal is to solve a problem, find an answer, understand a situation, and Geography offers unique tools for that as well. All problem solving is about breaking a complex problem into divisible, solvable units. For a geographer this starts with the application of spatial logic to the problem; this means when solving a multivariate problem, a geographer will accept the spatial distribution and spatial associations of a phenomenon as primary evidence, and then seek to discover the processes that led to that distribution. This contrasts most disciplines, where process based knowledge on individual characteristics are combined, then tested against the spatial distribution . The elevation of spatial logic over process logic is the key differentiator between a geographer and a domain-specific analyst.

Bringing spatial logic into the technological domain relies upon Geographic Information Science (GISc) to provide the conceptual framework, algorithms, and specialized tools needed to analyze data encoded with location information. It is the analytical power of these functions, integrated with the data collection, storage, retrieval and dissemination tools of GIS, that form the toolkit for problem solving used by geographers. Additionally, cartographic visualization provides a mechanism to encode these data and analysis so that complex spatio-temporal relationships can be displayed and quickly understood. Whether it is data exploration, sense making, or communicating results, displaying geographic data in map form is a tremendous advantage over text. And now with the web, cartography can be interactive, cross-multiple scales, and be dynamic through time.

So, why is now the time for geographers? The answer is threefold, first it has to do with the scale and complexity of problems we are facing, second is the amount and variety of information that can be applied to the problems, and third is the maturity of the digital geographic tools. Finding solutions to deal with climate change, energy, sustainable development, disaster risk reduction, and national security will require interdisciplinary approaches that are firmly grounded in the spatial dimension. With the transition to a digital world, society (governments included) finds itself in a state of information overload. In this world where data is plentiful, value shifts from acquiring data to understanding it. Geography as a discipline, and geographers equipped with a new generation of spatial information technology, are well adapted to this new paradigm.

If done correctly, the modern geographer has broad academic training across a range of disciplines, uses the spatial perspective as a means of information integration and analysis, and is facile with the digital tools needed to collect, store, analyze, visualize, and disseminate geographic information and analysis. Combine these skills with management and leadership training, and the geographer becomes a portent fusion. One that I think this article correctly identifies as critical to the leadership teams needed to solve big problems.

Here they come to save the day…

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Dobson, J. E. (1992). Spatial Logic in Paleogeography and the Explanation of Continental Drift. Annals of the Association of American Geographers, 82, 187–206.

In 2013, the NextGov media organization began the Bold Award, given for innovation in Federal technology. It is an interesting award, as the idea of innovation in the government is usually the punchline of a bad joke. But the folks at NextGov are on to something, as innovation in the government is actually really difficult. Besides the usual set of restrictions (a stodgy, risk-adverse bureaucracy, broken acquisition processes, and woefully dated information systems), one of the challenges is measuring the impact of an innovation.

In the private sector, a financial metric like Return on Investment (ROI) is a visceral and quantifiable measure of success. Usually a product is built to fill a gap identified in the market. In order to manage the risk of launching a new product, a protoype is built, beta tested, feedback from the market incorporated, and a revised prototype is built. Wash-Rinse-Repeat till the product makes money, or the underlying assumptions are proven wrong and development stops.

For several reasons the notion that an innovation could be proposed, implemented, measured, iterated, and the team rewarded for success does not translate to government. First, success is difficult to quantify, let alone tie back to specific actions. In the context of the HIU, what is the value of informing a policy maker better? How do you measure a good decision? How do you know its a good decision when you can’t know the alternative? When trying to build something like Imagery to the Crowd or the CyberGIS, how can I measure the impact on foreign policy? When a decision is ultimately made, it was on the basis of multiple streams of information, how do you determine the value of a single product? This situation is not unique to government, but the government does introduce some unique dynamics.

Second, there is no incentive to reduce cost. A culture of “we have money at the end of the year” means dollars get spent by years end, often regardless of utility. So if you actually save money, the bureaucracy figures you can do your mission for less and cuts your budget. This is a sentiment that is counter-intuitive at best, criminal at worst.

Third, the broken acquisition systems means that there is no way to fund an agile approach to product development in the government. Implementations of “minimal viable product” and rapid prototypes are a rare occurrence in the government. Instead, innovation must follow a procurement process where the innovator has to determine “requirements” (a mind-numbing process), put it out to bid (a mind-numbing process), idea awarded to low ball estimator, it gets built (maybe correctly), and two fiscal years after you started, you have some implementation of your innovative idea (that you have to pay extraordinary costs to the original contractor to change). Not a recipe for success.

We know government bureaucrats work for the citizens (something I was proud to do), and that they have a duty to reduce costs and increase the quality of services delivered to/for citizens. However, the system is broken when the momentum behind keeping the status quo in place massively overwhelms the need for change. So what exactly is the motivation for a government employee to be innovative? We know its not money, as innovators are worth significantly more in the private sector. From my experience it comes down to the fact that people care. Yeah, not usually a thought that people use to describe government bureaucrats, but it’s true. There is a tremendous amount of talent and willingness to work hard in the government workforce. The problem is they are shackled, and the cost to be innovative is a personal willingness to put themselves at risk and continually run through bureaucratic walls. As documented by the Washington Post lately, the government is losing the next generation of leaders because of this nonsense.

So back to the idea of awarding innovation in Federal technology. As part of the NextGov inaugural class, I was nominated and awarded a 2013 Bold Award for the Imagery to the Crowd initiative. This was an honor to win, but also disingenuous in that it would not have happened without a crew of people. Those folks at the HIU and elsewhere know who they are and the key role they played. Gratitude. #oMC.

Back in March 2014, FCW published two articles written by Frank Konkel that mentioned the HIU’s work with digital mapping. The first, entitled “Why Maps Matter“, is a good summary piece that reviews how geographic technology is used in various U.S. government agencies. The key points are the growing recognition in the government that visualization is a powerful tool for policy making, and how new companies are making it significantly easier for new users to leverage geographic technology. Beyond discussing the HIU, case studies from the Federal Communications Commission (FCC), Capitol Hill, National Park Service (NPS), and the National Geospatial-Intelligence Agency (NGA) are mentioned.

The second article, State Department: Mapping the humanitarian crisis in Syria, is a shorter piece that focuses solely on the HIU and its work in mapping the Syria humanitarian crisis. Having worked closely on Syria for two years, I can say we put a tremendous amount of effort into building comprehensive refugee datasets, verifying data from news reports, NGO reports, and commercial satellite imagery. Additionally we built inter-agency compatible data schema that leveraged geographic locations and P-Codes for information integration (P-Code dataset, P-Code Viewer). And to visualize it all, we built custom web mapping applications with tools to interactively explore all of the data across time and space. A significant portion of the HIU work on Syria (and now Iraq) is available on the HIU Middle East Products page, additionally, the data used for the Refugee and Internally Displaced Peoples layers are available for download on the HIU Data page.

It is clear the appreciation and value for geographical data, analysis, and visualization are on the rise; FCW lists the the Why Maps Matter article as the 3rd most popular of 2014. Fully recognizing the value of geography requires that the notion of maps as “pieces of paper” must be replaced with an appreciation and use of geographic data and spatial analysis as a tool of policy formation. This change is happening, albeit slower than I’d like, but its adoption will result in better, more agile policy, and benefit the government and citizens alike.

Clip of Syria map produced by the HIU, full map available here – https://hiu.state.gov/Products/Syria_DisplacementRefugees_2014Oct23_HIU_U1109.pdf

‘Disruption is a theory: a conceptual model of cause and effect that makes it possible to better predict the outcomes of competitive battles in different circumstances’ — The Innovators Solution

My PhD dissertation at the University of Kansas is entitled “The Disruptive Potential of GIS 2.0: An application in the humanitarian domain”. The research involves several interrelated philosophical, technological, and methodological components, but at its core, it is about building a new way to harness the power of geographic analysis. In short, the idea is to show how Geographic Information Systems (GIS) has evolved into something different than it was before, explore the dynamics of that evolution, then build new tools and methods that capitalize on those dynamics.

The foundation of the argument is that a new generation of digital geographic tools, defined here as GIS 2.0, have completely changed how core GIS processes are implemented. While the core functions of a GIS remain the same — the creation, storage, analysis, visualization, and dissemination of geographic data — the number of software packages capable of implementing spatial functions and the distribution capacity of the Internet have fundamentally changed the desktop GIS paradigm. Driving GIS 2.0 is a converging set of technology trends including open source software, decreasing computation costs, ubiquitous data networks, mobile phones, location-based services, spatial database, and cloud computing.The most significant, open source software, has dramatically expanded access to geographic data and spatial analysis by lowering the barrier to entry into geographic computing. This expansion is leading to a new set of business models and organizations built around geographic data and analysis. Understanding how and why these trends converged, and what it means for the future, requires a conceptual framework that embeds the ideas of the Open Source Paradigm Shift and Commons-based Peer Production within the larger context of Disruptive Innovation Theory .

While there is a philosophical element to this argument, the goal of the dissertation is to utilize the insights provided by disruptive innovation theory to build geographic systems and processes that can actually make a difference in how the humanitarian community responds to a complex emergency. It has been long recognized that geographic analysis can benefit the coordination and response to complex emergencies , yet the deployment of GIS has been hampered by a set of issues related to cost, training, data quality, and data collection standards . Using GIS 2.0 concepts there is an opportunity to overcome these issues, but doing so requires new technological and methodological approaches. With utility as a goal, the research is structured around general three sections:

GIS 2.0 Philosophy: Exploring the fundamental reorganization of GIS processes, and building a conceptual model, based on disruptive innovation theory, for explaining that evolution and predicting future changes

GIS 2.0 Methodology: Leverage the CyberGIS and GIS 2.0 concepts to build the “Imagery to the Crowd” process, a new methodology for crowdsourcing geographic data that can be deployed in a range of humanitarian applications

In the next series of posts I will explore each of the points above. My goal is to complete the dissertation in the coming months and I want to use this blog as a staging ground for drafts, chapters, and articles that can be submitted to my committee. As such they will likely be a bit rough. I am a perfectionist in my writing, which only serves to completely slow down my productivity, so hopefully this will force me to “release early and often.”

The core arguments of GIS 2.0 were originally conceived during 2006-2008, so they are a bit dated now. At the time there was really only anecdotal evidence to support the argument that the same Web 2.0 forces that built Wikipedia and disrupted the encyclopedia market were going to impact GIS. However, with the continued rise of FOSS4G, OpenStreetMap, and now the Humanitarian OpenStreetMap Team (HOT), it feels almost redundant to be making this argument now. Additionally, from the technology perspective there are lots of individuals and groups out there doing more cutting edge work than I ever will, but I hope the combination of philosophical approach and actual implementation can be a contribution to the discipline of geography — and more importantly, help the humanitarian community be more effective.

National Research Council. 2007. Successful response starts with a map: improving geospatial support for disaster management. Washington, D.C: National Academies Press.

O’Reilly, T. 2007. What is Web 2.0: Design Patterns and Business Models for the Next Generation of Software. Communications & Strategies 1:17. http://ssrn.com/abstract=1008839 (last accessed 22 January 2013).

Update: Both jobs have been filled (21 Sept 2013)

The Jobs

Available immediately, the U.S Department of State is looking to fill two positions related to geographic analysis and geographic programming. The Office of eDiplomacy, the State Department’s knowledge management gurus, want to build a first-rate geographic application development team. The two-person team will work with DoS bureaus to understand their workflows, leverage the geographic components of their data, and build custom geographic applications to help them. The team will be composed of one GIS applications developer, and one GIS analyst. Each position will require a substantial overlap in skills, meaning the developer must understand GIS analysis and the analyst will have to have some programming experience.

In that capacity, I started a project to build a completely open source geographic computing infrastructure focused on humanitarian applications. Called the CyberGIS, this project is built exclusively from open source geographic technology including, PostGIS/PostgreSQL, GeoServer, TileCache, OpenLayers, and TileMill, along with the standard Ubuntu, Apache, Tomcat, jQuery components, and we host our production environment in Amazon Web Services. Using the term CyberGIS was intentional and intended to place the project inline with on-going efforts in the academic community to unite the worlds of geographic information science and cyberinfrastructure.

We have used this infrastructure to build several HIU geographic web applications, including the Imagery to the Crowd projects. These award winning projects are just the beginning for the CyberGIS at the HIU, we have several applications under development that we hope to unveil publicly in the coming months. The success of the HIU CyberGIS has raised the attention of geography in the Department, and the fact that eDiplomacy is building this development team is a huge step in expanding the power of Geography to the entire State Department. Two years ago I could not have expected that we could move this far this fast, and now we have an opportunity to fundamentally influence how the Department operates.

The Ask

If you have serious GIS analysis and open source geographic developer skills and want to be part of a geographic revolution, then I encourage you to apply. We need forward leaning, capable folks who fundamentally understand spatial analysis and geographic technololgy. You must be willing to work hard and be leaders in showing how geographic data and analysis can improve American diplomacy. This is a unique moment and we need the right team.

However, I have a problem. I work in an organization where our primary product is a hard-copy map. As we evolve our product line, our challenge is to produce digital, interactive, web-enabled versions of our hard-copy map content and maintain a high-level of cartographic goodness. Our cartographic team works in Adobe Illustrator, and are quite proficient in it.

The problem we face is having to do cartographic work twice in order to switch between Illustrator and the Web. There has to be a better way. We are currently using TileMill for a significant amount of our web rendering, but also intend to transition to GeoServer. This means we have .AI, CartoCSS and .SLD in the mix.

We need to keep Illustrator as our foundation for creating content, so what is the best option to extend to the web? First is the problem of converting from .AI to CartoCSS, specifically the conversion of graphic styles for each Illustrator layer to its CartoCSS equivalent. I’ve never heard of a converter tool for this and am interested to know if anyone (@opengeo @ortelius @mapbox @ericg @tmcw @springmeyer @kelso @mattpriour…anyone at Adobe) has an idea if it is feasible or the amount of effort it would take.

Second is the problem of having to convert .AI to both CartoCSS for TileMill and SLD for GeoServer. The best option would be to have GeoServer consume CartoCSS natively, that way offline tiles and web services could maintain the same cartographic styling.

I posed similar questions on Twitter to @cageyjames and @spara, and @spara’s reply got me thinking whether I was looking at this question the wrong way. Is this too old school to be considering tools like this, so I wanted to know if anyone else had been thinking about it.

Thankfully @mattpriour replied that work was already being planned at OpenGeo to implement CartoCSS for GeoServer. And @godwinsgo also replied that GeoServer already has some form of CSS style rendering. So it looks like the CartoCSS in GeoServer has a chance of being completed, that just leaves the .AI to CartoCSS conversion.